A waterfront town with a pier, dock, and several buildings.

Beach Hotels in Chestertown, New York

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Check availability on Chestertown Beach Hotels

Our top choices for Chestertown beach hotels

Room

1. Friends Lake Inn

Friends Lake Inn
4.0 star property
Chestertown
8.6 out of 10, Excellent, (138 reviews)
"Great breakfast, very friendly staff and beautiful place"
United States
Pierre
The price is P5,717
P6,346 total
includes taxes & fees
Nov 15 - Nov 16
Friends Lake Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Choose what matters most at beach hotels in Chestertown

Pool
Breakfast included

Top Chestertown Hotel Reviews

Holiday Inn Resort Lake George - Adirondack Area by IHG

Holiday Inn Resort Lake George - Adirondack Area by IHG

10/10 Excellent
"Staff from TR's bar treat you like friends and family. All staff at the hotel were very attentive and pleasant. Cleanliness was good. Prices were higher than expected for a holiday in, but the world is getting too expensive. Great stay for the week."
James 7-night trip
Posted 6 hours ago
Holiday Inn Resort Lake George - Adirondack Area by IHG

Frequently asked questions

What is Chestertown like for travelers who love the beach?
Known for its lakeside setting, Chestertown offers a lot for the traveler planning a getaway.
What's the best accommodation to stay near the beach in Chestertown?
The Fern Lodge is a top beach B&B with free breakfast and 8 hot tubs, and it's located close to Loon Lake Beach.
When's the best time for a beach vacation in Chestertown?
Plan your trip to the beach with a look at the seasons in Chestertown: The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Chestertown are January, March, November, and December, with each month seeing an average of 13 inches of snowfall.
What is there to see and do around Chestertown?
After arriving and checking into your hotel, you'll probably want to explore your surroundings. If you're eager to check out the beaches, head to Veterans Memorial Park Beach or Rogers Memorial Park Beach for some relaxation by the water. Discover the area's lakeside setting, and make time for local attractions like Loon Lake Beach and Friends Lake. Other things to see and do in the area are Loon Lake and Hudson River.
What's the best way to get to my beach hotel in Chestertown?
Here's some information to help you get to and around your beach accommodation in Chestertown more easily: Make your way to Chestertown with a flight to Glens Falls, NY (GFL-Floyd Bennett Memorial), the closest major airport which is located 23.6 mi (38 km) from the city center. If you'd like to venture out around the area, you may want to rent a car for your trip.

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